Dimethylformamide → HCID 86591561, compound

HRID 1294126Notes

Reaction equation

HRID 1294126 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[OH:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]=1[CH:34]=[O:35].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:14][C:13]1[O:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:10][C:9]=1[CH2:8][O:7][C:6]1[CH:21]=[CH:22][C:3]([CH2:2][O:23][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:34]=[O:35])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 128192-Hydroxy-1-naphthaldehydeHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Product 1

HCID 86591561HCID 86591561, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (11.13 g), 2-hydroxy-1-naphthaldehyde (5.96 g), anhydrous potassium carbonate (5.03 g) and N,N-dimethylformamide (50 mL) was stirred at room temperature for 2 days. The reaction mixture was poured into water, and the precipitated solid was collected by filtration, and dried with air to give crystals (13.83 g, 89%) of 2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-1-naphthaldehyde. Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 141-142° C.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried with air

Sources & evidence

ORD record
ord-7539593945114c2abc81b9bd900a4f99
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…